Triethylamine → 2-Acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline

HRID 1014354노트

반응식

HRID 1014354 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH2:9][NH:8][CH2:7][CH2:6]2.[C:16](Cl)(=[O:19])[CH:17]=[CH2:18].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1.O>[C:16]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:9]1)(=[O:19])[CH:17]=[CH2:18]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 594418746-Methoxy-7-nitro-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 594417802-Acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline수율 84.2%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of 6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (1.6 g, 7.7 mmol) in dichloromethane (30 mL) was treated with acryloyl chloride (1.9 mL, 23 mmol, TCl), triethylamine (3.2 mL, 23 mmol, Aldrich), and catalytic 4-dimethylaminopyridine (50 mg 0.41 mmol, Aldrich). The mixture was stirred for 16 h, diluted with excess water, and extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, filtered, and concentrated to provide 2-acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (1.7 g, 84%). 1H NMR (400 MHz, DMSO-d6) is complicated due to amide rotomers δ ppm 2.86-2.95 (two triplets at 2.88 and 2.93, 2 H), 3.72-3.82 (two triplets at 3.74 and 3.80, 2 H), 3.89 (m, 3 H), 4.63-4.80 (two singlets at 4.65 and 4.77, 2 H), 5.73 (app d, J=10.3 Hz, 1 H), 6.16 (dd, J=16.7, 2.4 Hz, 1 H), 6.89 (dd, J=16.9, 10.3 Hz, 1 H), 7.21 (s, 1 H), 7.78-7.84 (two singlets at 7.79 and 7.83, 1 H); ESIMS (M+H)+=263.

후처리

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8cc9bedb7beb4f339b8310f7a67bc626
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981903B2

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